4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles

Yu P. Bandera; O. S. Kanishchev; V. M. Timoshenko; S. A. But; A. M. Nesterenko; Yu G. Shermolovich

doi:10.1007/s10593-007-0175-x

4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles

Yu P. Bandera, O. S. Kanishchev, V. M. Timoshenko, S. A. But, A. M. Nesterenko, Yu G. Shermolovich

Biochemistry & Molecular Biology

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

Treatment of 4-aryl(benzyl)sulfonyl-5-polyfluoroalkyl-v-triazoles with NaOCl gave the 4-aryl(benzyl)-sulfonyl-2-chloro-5-polyfluoroalkyl-v-triazole derivatives which contain a chlorine atom only on the N₍₂₎ atom of the heterocycle. The structure of 2-chloro-5-(1,1,2,2,3,3-hexafluoropropyl)-4- (p-tolyl-sulfonyl)-2H-[1,2,3]triazole has been established by X-ray structural investigation. The presence of a highly polarized N-Cl bond with a positive halogen atom causes the N-chlorotriazoles to react with KCN and KF as strong acids to form the potassium salts of the triazoles and to form 4-arylsulfonyl-2-(2-chloro-1-ethoxyethyl)-5-polyfluoroalkyl-2H-[1,2,3]triazoles with vinyl ethyl ether. It was found that chlorination of 4-arylsulfonyl-5- polyfluoroalkyl-v-triazoles in the presence of KF gives 4-chloro-5- polyfluoroalkyl-2H-[1,2,3]triazoles.

Original language	English (US)
Pages (from-to)	1138-1147
Number of pages	10
Journal	Chemistry of Heterocyclic Compounds
Volume	43
Issue number	9
DOIs	https://doi.org/10.1007/s10593-007-0175-x
State	Published - Sep 1 2007

Keywords

1,1-dihydropolyfluoroalkyl sulfone
N-chlorotriazole
V-triazole
X-ay structural analysis

ASJC Scopus subject areas

Organic Chemistry

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4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles. / Bandera, Yu P.; Kanishchev, O. S.; Timoshenko, V. M.; But, S. A.; Nesterenko, A. M.; Shermolovich, Yu G.

In: Chemistry of Heterocyclic Compounds, Vol. 43, No. 9, 01.09.2007, p. 1138-1147.

Research output: Contribution to journal › Article › peer-review

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title = "4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles",

abstract = "Treatment of 4-aryl(benzyl)sulfonyl-5-polyfluoroalkyl-v-triazoles with NaOCl gave the 4-aryl(benzyl)-sulfonyl-2-chloro-5-polyfluoroalkyl-v-triazole derivatives which contain a chlorine atom only on the N(2) atom of the heterocycle. The structure of 2-chloro-5-(1,1,2,2,3,3-hexafluoropropyl)-4- (p-tolyl-sulfonyl)-2H-[1,2,3]triazole has been established by X-ray structural investigation. The presence of a highly polarized N-Cl bond with a positive halogen atom causes the N-chlorotriazoles to react with KCN and KF as strong acids to form the potassium salts of the triazoles and to form 4-arylsulfonyl-2-(2-chloro-1-ethoxyethyl)-5-polyfluoroalkyl-2H-[1,2,3]triazoles with vinyl ethyl ether. It was found that chlorination of 4-arylsulfonyl-5- polyfluoroalkyl-v-triazoles in the presence of KF gives 4-chloro-5- polyfluoroalkyl-2H-[1,2,3]triazoles.",

keywords = "1,1-dihydropolyfluoroalkyl sulfone, N-chlorotriazole, V-triazole, X-ay structural analysis",

author = "Bandera, {Yu P.} and Kanishchev, {O. S.} and Timoshenko, {V. M.} and But, {S. A.} and Nesterenko, {A. M.} and Shermolovich, {Yu G.}",

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AU - Bandera, Yu P.

AU - Kanishchev, O. S.

AU - Timoshenko, V. M.

AU - But, S. A.

AU - Nesterenko, A. M.

AU - Shermolovich, Yu G.

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N2 - Treatment of 4-aryl(benzyl)sulfonyl-5-polyfluoroalkyl-v-triazoles with NaOCl gave the 4-aryl(benzyl)-sulfonyl-2-chloro-5-polyfluoroalkyl-v-triazole derivatives which contain a chlorine atom only on the N(2) atom of the heterocycle. The structure of 2-chloro-5-(1,1,2,2,3,3-hexafluoropropyl)-4- (p-tolyl-sulfonyl)-2H-[1,2,3]triazole has been established by X-ray structural investigation. The presence of a highly polarized N-Cl bond with a positive halogen atom causes the N-chlorotriazoles to react with KCN and KF as strong acids to form the potassium salts of the triazoles and to form 4-arylsulfonyl-2-(2-chloro-1-ethoxyethyl)-5-polyfluoroalkyl-2H-[1,2,3]triazoles with vinyl ethyl ether. It was found that chlorination of 4-arylsulfonyl-5- polyfluoroalkyl-v-triazoles in the presence of KF gives 4-chloro-5- polyfluoroalkyl-2H-[1,2,3]triazoles.

AB - Treatment of 4-aryl(benzyl)sulfonyl-5-polyfluoroalkyl-v-triazoles with NaOCl gave the 4-aryl(benzyl)-sulfonyl-2-chloro-5-polyfluoroalkyl-v-triazole derivatives which contain a chlorine atom only on the N(2) atom of the heterocycle. The structure of 2-chloro-5-(1,1,2,2,3,3-hexafluoropropyl)-4- (p-tolyl-sulfonyl)-2H-[1,2,3]triazole has been established by X-ray structural investigation. The presence of a highly polarized N-Cl bond with a positive halogen atom causes the N-chlorotriazoles to react with KCN and KF as strong acids to form the potassium salts of the triazoles and to form 4-arylsulfonyl-2-(2-chloro-1-ethoxyethyl)-5-polyfluoroalkyl-2H-[1,2,3]triazoles with vinyl ethyl ether. It was found that chlorination of 4-arylsulfonyl-5- polyfluoroalkyl-v-triazoles in the presence of KF gives 4-chloro-5- polyfluoroalkyl-2H-[1,2,3]triazoles.

KW - 1,1-dihydropolyfluoroalkyl sulfone

KW - N-chlorotriazole

KW - V-triazole

KW - X-ay structural analysis

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4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles

Abstract

Keywords

ASJC Scopus subject areas

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